Emails stopped working, failing after upgrade

Product Support Self-hosting

AI-generated summary

After upgrading to Discourse 2.9.0 beta4, emails began failing due to SSL-related issues when using Ehlo as an SMTP to HTTP gateway. The user reports that the site is fully SSL, but the SMTP client requires non-SSL, which has worked for two years until this upgrade. The error indicates an SSL handshake failure with a ‘tlsv1 alert unknown ca’ error, suggesting a certificate mismatch. sok777 seeks help, noting the issue may relate to recent changes in SSL handling. JammyDodger references a related support topic on certificate mismatches that might provide a solution.

1

After upgrading to 2.9.0 beta4, our emails started failing.

Is there a major change to cause that? It seems the issue is with SSL?
We use Ehlo as SMTP to HTTP gateway

The site is fully SSL but we need the SMTP client side of discourse to be non-SSL for this to work. It’s been working perfectly for the past 2 years until this upgrade.

Anything that can cause that? I’ve spent hours trying to find a solution on existing posts but couldn’t find anything.


discourse-ubuntu:~$ /usr/local/bin/ehlo -p 2525 -a https://appspot.com/meet
2022-05-19T13:53:23.504Z - info: Starting ehlo
2022-05-19T13:53:23.515Z - info: Listening on port [2525]
events.js:183
      throw er; // Unhandled 'error' event
      ^

Error: 140277961931648:error:14094418:SSL routines:ssl3_read_bytes:tlsv1 alert unknown ca:s3_pkt.c:1500:SSL alert number 48
140277961931648:error:140940E5:SSL routines:ssl3_read_bytes:ssl handshake failure:s3_pkt.c:1217
3

There was a recent support topic about Certificate mismatches that may have some useful information in? Email Hostname Certificate Mismatch Causing sidekiq Queue Overload, Severe Site Instability - #8 by RGJ